Reaxys
PubChem
eMolecules
Reactions (30)
Yield
Substances (11)
Citations (9)
Conditions
References
1
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Rx-ID: 1845249 Find similar reactions
With sodium hydride
1.) DMF, ice-bath, 2.) room temperature; Yield given. Multistep reaction;
2
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Schwartz, John A.
Synthetic Communications, 1986 , vol. 16, # 5 p. 565 - 570 Title/Abstract Full Text Show Details
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Rx-ID: 4303424 Find similar reactions
(i) SnCl4, CH2Cl2, (ii) H2O; Multistep reaction;
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Nichols; Shulgin
Journal of Pharmaceutical Sciences, 1976 , vol. 65, # 10 p. 1554 - 1556 Title/Abstract Full Text View citing articles Show Details
3
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Rx-ID: 4323547 Find similar reactions
73%
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Stage #1: N-methyl-N-formyl-aniline With trichlorophosphate
T=40 - 50°C; Vilsmeier reaction; Stage #2: 1,4-dimethoxy-2-methylthiobenzene T=70°C; 0.25 h;
Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.
Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details
With trichlorophosphate
Jacob III; Anderson III; Meshul; Shulgin; Castagnoli Jr.
Journal of Medicinal Chemistry, 1977 , vol. 20, # 10 p. 1235 - 1239 Title/Abstract Full Text View citing articles Show Details
4
Synthesize Find similar entspr. 'Benzol', Dichlormethylmethylether;
Rx-ID: 7365217 Find similar reactions
Bristol Myers
Patent: US4105695 , 1978 ; Full Text Show Details
5
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6
Multi-step reaction with 2 steps 1.1: KOH / methanol / 1 h 1.2: 99 percent / methanol / 0.5 h / Heating 2.1: POCl3 / 40 - 50 °C 2.2: 73 percent / 0.25 h / 70 °C View Scheme
Rx-ID: 13087849 Find similar reactions
Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.
Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details
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7
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Rx-ID: 13091243 Find similar reactions
Multi-step reaction with 3 steps 1.1: 99 percent / Zn; aq. HCl 2.1: KOH / methanol / 1 h 2.2: 99 percent / methanol / 0.5 h / Heating 3.1: POCl3 / 40 - 50 °C 3.2: 73 percent / 0.25 h / 70 °C View Scheme
Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.
Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 3 steps 1: Zn, H2SO4
2: (i) KOH, EtOH, (ii) /BRN= 969135/ 3: POCl3
View Scheme
Jacob III; Anderson III; Meshul; Shulgin; Castagnoli Jr.
Journal of Medicinal Chemistry, 1977 , vol. 20, # 10 p. 1235 - 1239 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 13100857 Find similar reactions
8
Multi-step reaction with 4 steps 1.1: 68.3 percent / aq. HOSO2Cl 2.1: 99 percent / Zn; aq. HCl 3.1: KOH / methanol / 1 h 3.2: 99 percent / methanol / 0.5 h / Heating 4.1: POCl3 / 40 - 50 °C 4.2: 73 percent / 0.25 h / 70 °C View Scheme
Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.
Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 4 steps 1: ClSO3H / CH2Cl2
2: Zn, H2SO4
3: (i) KOH, EtOH, (ii) /BRN= 969135/ 4: POCl3
View Scheme
Jacob III; Anderson III; Meshul; Shulgin; Castagnoli Jr.
Journal of Medicinal Chemistry, 1977 , vol. 20, # 10 p. 1235 - 1239 Title/Abstract Full Text View citing articles Show Details
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9
Multi-step reaction with 2 steps 1: (i) KOH, EtOH, (ii) /BRN= 969135/ 2: POCl3
View Scheme
Rx-ID: 22644279 Find similar reactions
Jacob III; Anderson III; Meshul; Shulgin; Castagnoli Jr.
Journal of Medicinal Chemistry, 1977 , vol. 20, # 10 p. 1235 - 1239 Title/Abstract Full Text View citing articles Show Details
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Multi-step reaction with 2 steps 1: caesium carbonate / DMFA / 12 h / 40 °C 2: phosphoryl chloride / 12 h / 90 °C View Scheme
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Rx-ID: 39719284 Find similar reactions
Huang, Yi-Chao; Guan, Chao-Jian; Tan, Xiang-Long; Chen, Chen-Chen; Guo, Qing-Xiang; Li, Yi-Ming
Organic and Biomolecular Chemistry, 2015 , vol. 13, # 5 p. 1500 - 1506 Title/Abstract Full Text View citing articles Show Details
10
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Rx-ID: 39719306 Find similar reactions
With phosphoryl chloride
T=90°C; 12 h;
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Huang, Yi-Chao; Guan, Chao-Jian; Tan, Xiang-Long; Chen, Chen-Chen; Guo, Qing-Xiang; Li, Yi-Ming
Organic and Biomolecular Chemistry, 2015 , vol. 13, # 5 p. 1500 - 1506 Title/Abstract Full Text View citing articles Show Details
11
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Rx-ID: 9146404 Find similar reactions
79%
With trichlorophosphate
With trichlorophosphate
T=100°C; 0.333333 h;
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Rezende, Marcos Caroli; Nunez, Christian; Sepulveda-Boza, Silvia; Cassels, Bruce K.; Hurtado-Guzman, Claudio
Synthetic Communications, 2002 , vol. 32, # 17 p. 2741 - 2750 Title/Abstract Full Text View citing articles Show Details
Xu, Ya-Zhu; Chen, Chinpiao
Journal of Labelled Compounds and Radiopharmaceuticals, 2006 , vol. 49, # 13 p. 1187 - 1200 Title/Abstract Full Text View citing articles Show Details
12
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Rx-ID: 9895373 Find similar reactions
88%
Stage #1: N-methyl-N-formyl-aniline With
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Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.;
trichlorophosphate
T=40 - 50°C; Vilsmeier reaction; Stage #2: 2-ethylsulfanyl-1,4-dimethoxybenzene T=70°C; 0.25 h;
Reyes-Parada, Miguel; Nichols, David E.
Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details
13
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Multi-step reaction with 2 steps 1: 86 percent / NaOH 2: 79 percent / POCl3
View Scheme
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Rx-ID: 14690105 Find similar reactions
Rezende, Marcos Caroli; Nunez, Christian; Sepulveda-Boza, Silvia; Cassels, Bruce K.; Hurtado-Guzman, Claudio
Synthetic Communications, 2002 , vol. 32, # 17 p. 2741 - 2750 Title/Abstract Full Text View citing articles Show Details
14
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Multi-step reaction with 3 steps 1.1: HSO3Cl 1.2: Zn; HCl 2.1: 86 percent / NaOH 3.1: 79 percent / POCl3
View Scheme
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Rx-ID: 14702999 Find similar reactions
Rezende, Marcos Caroli; Nunez, Christian; Sepulveda-Boza, Silvia; Cassels, Bruce K.; Hurtado-Guzman, Claudio
Synthetic Communications, 2002 , vol. 32, # 17 p. 2741 - 2750 Title/Abstract Full Text View citing articles Show Details
15
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Rx-ID: 11289597 Find similar reactions
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94%
With trichlorophosphate
T=100°C; 0.333333 h;
Xu, Ya-Zhu; Chen, Chinpiao
Journal of Labelled Compounds and Radiopharmaceuticals, 2006 , vol. 49, # 13 p. 1187 - 1200 Title/Abstract Full Text View citing articles Show Details
16
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Rx-ID: 9895376 Find similar reactions
78%
Stage #1: N-methyl-N-formyl-aniline With trichlorophosphate
T=40 - 50°C; Vilsmeier reaction; Stage #2: 1,4-dimethoxy-2-i-propylthiobenzene T=70°C; 0.25 h;
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Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.
Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details
17
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Rx-ID: 9895377 Find similar reactions
99%
Stage #1: N-methyl-N-formyl-aniline With trichlorophosphate
T=40 - 50°C; Vilsmeier reaction; Stage #2: 1,4-dimethoxy-2-(propylsulfanyl)benzene T=70°C; 0.25 h;
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Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.
Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details
18
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Rx-ID: 11289599 Find similar reactions
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With trichlorophosphate
T=100°C; 0.333333 h;
Xu, Ya-Zhu; Chen, Chinpiao
Journal of Labelled Compounds and Radiopharmaceuticals, 2006 , vol. 49, # 13 p. 1187 - 1200 Title/Abstract Full Text View citing articles Show Details
19
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Rx-ID: 11289598 Find similar reactions
86%
With trichlorophosphate
T=100°C; 0.333333 h;
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Xu, Ya-Zhu; Chen, Chinpiao
Journal of Labelled Compounds and Radiopharmaceuticals, 2006 , vol. 49, # 13 p. 1187 - 1200 Title/Abstract Full Text View citing articles Show Details
20
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Rx-ID: 9476346 Find similar reactions
86%
Stage #1: With trichlorophosphate
T=15 - 60°C; Vilsmeier-formylation; Stage #2: With water
0.5 h;
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Trachsel, Daniel
Helvetica Chimica Acta, 2003 , vol. 86, # 7 p. 2610 - 2619 Title/Abstract Full Text View citing articles Show Details
21
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Rx-ID: 9476347 Find similar reactions
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86%
Stage #1: N-methyl-N-formyl-aniline With trichlorophosphate
T=40 - 50°C; Vilsmeier reaction; Stage #2: 1,4-dimethoxy-2-n-butylthiobenzene T=70°C; 0.25 h;
Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.
Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details
85%
Stage #1: With trichlorophosphate
T=15 - 60°C; Vilsmeier-formylation; Stage #2: With water
0.5 h;
Trachsel, Daniel
Helvetica Chimica Acta, 2003 , vol. 86, # 7 p. 2610 - 2619 Title/Abstract Full Text View citing articles Show Details
22
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Multi-step reaction with 2 steps 1.1: KOH / methanol / 1 h 1.2: 96 percent / methanol / 0.5 h / Heating 2.1: POCl3 / 40 - 50 °C 2.2: 86 percent / 0.25 h / 70 °C View Scheme
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Rx-ID: 13087852 Find similar reactions
Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.
Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details
23
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24
Multi-step reaction with 3 steps 1.1: 99 percent / Zn; aq. HCl 2.1: KOH / methanol / 1 h 2.2: 96 percent / methanol / 0.5 h / Heating 3.1: POCl3 / 40 - 50 °C 3.2: 86 percent / 0.25 h / 70 °C View Scheme
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Rx-ID: 13091248 Find similar reactions
Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.
Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details
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Multi-step reaction with 4 steps 1.1: 68.3 percent / aq. HOSO2Cl 2.1: 99 percent / Zn; aq. HCl 3.1: KOH / methanol / 1 h 3.2: 96 percent / methanol / 0.5 h / Heating 4.1: POCl3 / 40 - 50 °C 4.2: 86 percent / 0.25 h / 70 °C View Scheme
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Rx-ID: 13100862 Find similar reactions
Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.
Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details
25
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Multi-step reaction with 2 steps 1.1: 90 percent / KOH / methanol / 1 h / Heating 2.1: POCl3 / 15 - 60 °C 2.2: 86 percent / H2O / 0.5 h View Scheme
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Rx-ID: 13992215 Find similar reactions
Trachsel, Daniel
Helvetica Chimica Acta, 2003 , vol. 86, # 7 p. 2610 - 2619 Title/Abstract Full Text View citing articles Show Details
26
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Multi-step reaction with 2 steps 1.1: 90 percent / KOH / methanol / 1 h / Heating 2.1: POCl3 / 15 - 60 °C 2.2: 85 percent / H2O / 0.5 h View Scheme
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Rx-ID: 13992216 Find similar reactions
Trachsel, Daniel
Helvetica Chimica Acta, 2003 , vol. 86, # 7 p. 2610 - 2619 Title/Abstract Full Text View citing articles Show Details
27
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Rx-ID: 9895375 Find similar reactions
99%
Stage #1: N-methyl-N-formyl-aniline With trichlorophosphate
T=40 - 50°C; Vilsmeier reaction; Stage #2: 1,4-dimethoxy-2-(pentylthio)benzene T=70°C; 0.25 h;
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Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.
Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details
28
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Multi-step reaction with 2 steps 1.1: KOH / methanol / 1 h 1.2: 99 percent / methanol / 0.5 h / Heating 2.1: POCl3 / 40 - 50 °C 2.2: 99 percent / 0.25 h / 70 °C View Scheme
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Rx-ID: 13087838 Find similar reactions
Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.
Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details
29
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Multi-step reaction with 3 steps 1.1: 99 percent / Zn; aq. HCl 2.1: KOH / methanol / 1 h 2.2: 99 percent / methanol / 0.5 h / Heating
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Rx-ID: 13091231 Find similar reactions
Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.
Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details
3.1: POCl3 / 40 - 50 °C 3.2: 99 percent / 0.25 h / 70 °C View Scheme
30
Synthesize Find similar Multi-step reaction with 4 steps 1.1: 68.3 percent / aq. HOSO2Cl 2.1: 99 percent / Zn; aq. HCl 3.1: KOH / methanol / 1 h 3.2: 99 percent / methanol / 0.5 h / Heating 4.1: POCl3 / 40 - 50 °C 4.2: 99 percent / 0.25 h / 70 °C View Scheme
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Rx-ID: 13100841 Find similar reactions
Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.
Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details